Combating fungi with N-allenyl-acetanilides

ABSTRACT

N-allenyl-acetanilides of the formula ##STR1## in which R 1  represents hydrogen, alkyl or halogen, 
     R 2  represents hydrogen or alkyl, 
     R 3  represents hydrogen or alkyl, 
     R 4  represents hydrogen or alkyl, 
     R 5  represents hydrogen or alkyl and 
     R 6  represents furyl, tetrahydrofuryl, thiophenyl or tetrahydrothiophenyl; isoxazolyl which is optionally substituted by alkyl; alkyl, alkenyl or alkynyl, in each case optionally substituted by cyano or thiocyano; dihalogenoalkyl; or the grouping ##STR2## wherein R 7  represents an optionally substituted alkyl, alkenyl, alkynyl or alkoxyalkyl radical and 
     Az represents pyrazol-1-yl, 1,2,4-triazol-1-yl or imidazol-1-yl. 
     which possess fungicidal properties.

This is a division, of application Ser. No. 136,026 filed Mar. 31, 1980,now U.S. Pat. No. 4,385,069.

The present invention relates to certain new N-allenyl-acetanilides, toa process for their preparation and to their use as fungicides.

It has already been disclosed that such halogenoacetanilides as, forexample, N-chloroacetyl-N-(2,6-dialkylphenyl)-alanine alkyl esters and-glycine alkyl esters can be employed with good success for combatingfungal diseases of plants (see DI-OS (German Published Specification)No. 2,350,944 and U.S. Pat. No. 3,780,090). However, their action is notalways completely satisfactory, especially when small amounts and lowconcentrations are used and in particular also when combatingPhytophthora species.

The present invention now provides, as new compounds, theN-allenyl-acetanilides of the general formula ##STR3## in which R¹represents hydrogen, alkyl or halogen,

R² represents hydrogen or alkyl,

R³ represents hydrogen or alkyl,

R⁴ represents hydrogen or alkyl,

R⁵ represents hydrogen or alkyl and

R⁶ represents furyl, tetrahydrofuryl, thiophenyl ortetrahydrothiophenyl; isoxazolyl which is optionally substituted byalkyl; alkyl, alkenyl or alkynyl, in each case optionally substituted bycyano or thiocyano; dihalogenoalkyl; or the grouping ##STR4## wherein R⁷represents an optionally substituted alkyl, alkenyl, alkynyl oralkoxyalkyl radical and

Az represents pyrazol-1-yl, 1,2,4-triazol-1-yl or imidazol-1-yl.

It has been found that the N-allenyl-acetanilides of the formula (I)have powerful fungicidal properties. Surprisingly, the compoundsaccording to the invention exhibit a considerably higher action,especially against Phytophthora, than theN-chloroacetyl-N-(2,6-dialkylphenyl)alanine alkyl esters and -glycinealkyl esters known from the state of the art.

Preferred compounds of the formula (I) are those in which R², R³, R⁴ andR⁵ are selected independently and each represent hydrogen orstraight-chain or branched alkyl with 1 to 4 carbon atoms;

R¹ represents hydrogen, straight-chain or branched alkyl with 1 to 4carbon atoms or halogen (especially fluorine, chlorine or bromine),

R⁶ represents furyl, tetrahydrofuryl, thiophenyl, tetrahydrothiophenyl;isoxazolyl which is optionally substituted by methyl or ethyl; alkylwith 1 to 4 carbon atoms or alkenyl or alkynyl with in either case 2 to4 carbon atoms, in each case optionally substituted by cyano orthiocyano; dihalogenoalkyl with 1 to 2 carbon atoms (preferred halogenatoms being fluorine and chlorine); or the grouping ##STR5##

Az represents pyrazol-1-yl, 1,2,4-triazol-1-yl or imidazol-1-yl; and

R⁷ represents alkyl with 1 to 4 carbon atoms or alkenyl or alkynyl within either case 2 to 4 carbon atoms, in each case optionally substitutedby halogen (especially fluorine, chlorine or bromine), cyano orthiocyano, or represents alkoxyalkyl with 1 to 4 carbon atoms in eachalkyl part.

Those substituted N-propargyl-anilines of the formula (I) are veryparticularly preferred in which R¹ represents hydrogen, methyl, ethyl,isopropyl, sec.-butyl, tert.-butyl, chlorine or bromine; R² and R³represent hydrogen, methyl, ethyl, isopropyl, sec.-butyl or tert.-butyl;R⁴ and R⁵ represent hydrogen, methyl or ethyl; and R⁶ represents2-furyl, 2-thienyl, 2-tetrahydrofuryl, vinyl, 5-methylisoxazol-3-yl,methoxymethyl, ethoxymethyl, allyloxymethyl, propargyloxymethyl,ethoxymethoxymethyl, methylmercaptomethyl, methoxy, ethoxy,methylmercapto, methylsulphonyloxymethyl, methoxycarbonyl,ethoxycarbonyl, propargyloxycarbonyl, dichloromethyl,pyrazol-1-yl-methyl, imidazol-1-yl-methyl, 1,2,4-triazol-1-yl-methyl ortetrahydropyran-2-yl-oxymethyl.

The following compounds of the general formula (I) may be mentionedspecifically, in addition to the compounds mentioned later in thepreparative examples:

    __________________________________________________________________________     ##STR6##                            (I)                                      R.sup.1                                                                             R.sup.2                                                                            R.sup.3                                                                            R.sup.4                                                                           R.sup.5                                                                           R.sup.6                                               __________________________________________________________________________    CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   H                                                                                  ##STR7##                                             CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   H                                                                                  ##STR8##                                             CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   H   CH.sub.2OCH.sub.2OC.sub.2 H.sub.5                     CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   H                                                                                  ##STR9##                                             CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   H                                                                                  ##STR10##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   H                                                                                  ##STR11##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   H                                                                                  ##STR12##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   H   CH.sub.2SCH.sub.3                                     CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   H   CH.sub.2SC.sub.2 H.sub.5                              CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   H   CHCl.sub.2                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   H   COOCH.sub.3                                           CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   H   CH.sub.2OSO.sub.2 CH.sub.3                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   H   COOCH.sub.2CCH                                        CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   H   CHCH.sub.2                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H                                                                                  ##STR13##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H   CH.sub.2OCH.sub.3                                     CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H                                                                                  ##STR14##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H                                                                                  ##STR15##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H                                                                                  ##STR16##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H   CH.sub.2OC.sub.2 H.sub.5                              CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H   CH.sub.2OCH.sub.2OC.sub.2 H.sub.5                     CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H                                                                                  ##STR17##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H                                                                                  ##STR18##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H                                                                                  ##STR19##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H                                                                                  ##STR20##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H   CH.sub.2SCH.sub.3                                     CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H   CH.sub.2SC.sub.2 H.sub.5                              CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H   CHCl.sub.2                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H   COOCH.sub.3                                           CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H   CH.sub.2 OSO.sub.2 CH.sub.3                           CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H   COOCH.sub.2CCH                                        CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          H   CHCH.sub.2                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                           ##STR21##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                          CH.sub.2OCH.sub.3                                     CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                           ##STR22##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                           ##STR23##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                           ##STR24##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                          CH.sub.2OC.sub.2 H.sub.5                              CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                          CH.sub.2OCH.sub.2OC.sub.2 H.sub.5                     CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                           ##STR25##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                           ##STR26##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                           ##STR27##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                           ##STR28##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                          CH.sub.2SCH.sub.3                                     CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                          CH.sub.2SC.sub.2 H.sub.5                              CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                          CHCl.sub.2                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                          COOCH.sub.3                                           CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                          CH.sub.2OSO.sub.2 CH.sub.3                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                          COOCH.sub.2CCH                                        CH.sub.3                                                                            6-CH.sub.3                                                                         H    H   CH.sub.3                                                                          CHCH.sub.2                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                           ##STR29##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.2OCH.sub.3                                     CH.sub.3                                                                            6-CH.sub. 3                                                                        H    CH.sub.3                                                                          CH.sub.3                                                                           ##STR30##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                           ##STR31##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                           ##STR32##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.2OC.sub.2 H.sub.5                              CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.2OCH.sub.2OC.sub.2 H.sub.5                     CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                           ##STR33##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                           ##STR34##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                           ##STR35##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                           ##STR36##                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub. 3                                                                         CH.sub.3                                                                          CH.sub.2SCH.sub.3                                     CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.2SC.sub.2 H.sub.5                              CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                          CHCl.sub.2                                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                          COOCH.sub.3                                           CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.2OSO.sub.2 CH.sub.3                            CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                          COOCH.sub.2CCH                                        CH.sub.3                                                                            6-CH.sub.3                                                                         H    CH.sub.3                                                                          CH.sub.3                                                                          CHCH.sub.2                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   H                                                                                  ##STR37##                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   H   CH.sub.2OCH.sub.3                                     CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   H                                                                                  ##STR38##                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   H                                                                                  ##STR39##                                            CH.sub.3                                                                            6-C.sub.2 H.sub. 5                                                                 H    H   H   CH.sub.2OC.sub.2 H.sub.5                              CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   H   CH.sub.2OSO.sub.2 CH.sub.3                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   H   CHCl.sub.2                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   H   COOCH.sub.3                                           CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   H                                                                                  ##STR40##                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   H   CH.sub.2SCH.sub.3                                     CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   H                                                                                  ##STR41##                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   H   CHCH.sub.2                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H                                                                                  ##STR42##                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H   CH.sub.2OCH.sub.3                                     CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H                                                                                  ##STR43##                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H                                                                                  ##STR44##                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H   CH.sub.2OC.sub.2 H.sub.5                              CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H   CH.sub.2OSO.sub.2 CH.sub.3                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H   CHCl.sub.2                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H   COOCH.sub.3                                           CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H                                                                                  ##STR45##                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H   CH.sub.2SCH.sub.3                                     CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H                                                                                  ##STR46##                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H   CHCH.sub.2                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                           ##STR47##                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                          CH.sub.2OCH.sub.3                                     CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                           ##STR48##                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                           ##STR49##                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                          CH.sub.2OC.sub.2 H.sub.5                              CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                          CH.sub.2OSO.sub.2 CH.sub.3                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                          CHCl.sub.2                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                          COOCH.sub.3                                           CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                           ##STR50##                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                          CH.sub.2SCH.sub.3                                     CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                           ##STR51##                                            CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                          CHCH.sub.2                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   H                                                                                  ##STR52##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   H   CH.sub.2OCH.sub.3                                     C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   H                                                                                  ##STR53##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   H                                                                                  ##STR54##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   H   CH.sub.2OC.sub.2 H.sub.5                              C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   H   CH.sub.2OSO.sub.2 CH.sub.3                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   H   CHCl.sub.2                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   H   COOCH.sub.3                                           C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   H                                                                                  ##STR55##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   H   CH.sub.2SCH.sub.3                                     C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   H                                                                                  ##STR56##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   H   CHCH.sub.2                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H                                                                                  ##STR57##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H   CH.sub.2OCH.sub.3                                     C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H                                                                                  ##STR58##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H                                                                                  ##STR59##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H   CH.sub.2OC.sub.2 H.sub.5                              C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H   CH.sub.2OSO.sub.2 CH.sub.3                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H   CHCl.sub.2                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    CH.sub. 3                                                                         H   COOCH.sub.3                                           C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H                                                                                  ##STR60##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H   CH.sub.2SCH.sub.3                                     C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H                                                                                  ##STR61##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    CH.sub.3                                                                          H   CHCH.sub.2                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                           ##STR62##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                          CH.sub.2OCH.sub.3                                     C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                           ##STR63##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                           ##STR64##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                          CH.sub.2OC.sub.2 H.sub.5                              C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                          CH.sub.2OSO.sub.2 CH.sub.3                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                          CHCl.sub.2                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                          COOCH.sub.3                                           C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                           ##STR65##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                          CH.sub.2SCH.sub.3                                     C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                           ##STR66##                                            C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                  H    H   CH.sub.3                                                                          CHCH.sub.2                                            C(CH.sub.3).sub.3                                                                   H    H    H   H                                                                                  ##STR67##                                            C(CH.sub.3).sub.3                                                                   H    H    H   H   CH.sub.2OCH.sub.3                                     C(CH.sub.3).sub.3                                                                   H    H    H   H                                                                                  ##STR68##                                            C(CH.sub.3).sub.3                                                                   H    H    H   H                                                                                  ##STR69##                                            C(CH.sub.3).sub.3                                                                   H    H    H   H   CH.sub.2OC.sub.2 H.sub.5                              C(CH.sub.3).sub.3                                                                   H    H    H   H   CH.sub.2OSO.sub.2 CH.sub.3                            C(CH.sub.3).sub.3                                                                   H    H    H   H   CHCl.sub.2                                            C(CH.sub.3).sub.3                                                                   H    H    H   H   COOCH.sub.3                                           C(CH.sub.3).sub.3                                                                   H    H    H   H                                                                                  ##STR70##                                            C(CH.sub.3).sub.3                                                                   H    H    H   H   CH.sub.2SCH.sub.3                                     C(CH.sub.3).sub.3                                                                   H    H    H   H                                                                                  ##STR71##                                            C(CH.sub.3).sub.3                                                                   H    H    H   H   CHCH.sub.2                                            Cl    6-CH.sub.3                                                                         H    H   H                                                                                  ##STR72##                                            Cl    6-CH.sub.3                                                                         H    H   H   CH.sub.2OCH.sub.3                                     Cl    6-CH.sub.3                                                                         H    H   H                                                                                  ##STR73##                                            Cl    6-CH.sub.3                                                                         H    H   H                                                                                  ##STR74##                                            Cl    6-CH.sub.3                                                                         H    H   H   CH.sub.2OC.sub.2 H.sub.5                              Cl    6-CH.sub.3                                                                         H    H   H   CH.sub.2OSO.sub.2 CH.sub.3                            Cl    6-CH.sub.3                                                                         H    H   H   CHCl.sub.2                                            Cl    6-CH.sub.3                                                                         H    H   H   COOCH.sub.3                                           Cl    6-CH.sub.3                                                                         H    H   H                                                                                  ##STR75##                                            Cl    6-CH.sub.3                                                                         H    H   H   CH.sub.2SCH.sub.3                                     Cl    6-CH.sub.3                                                                         H    H   H                                                                                  ##STR76##                                            Cl    6-CH.sub.3                                                                         H    H   H   CHCH.sub.2                                            CH.sub.3                                                                            3-CH.sub.3                                                                         6-CH.sub.3                                                                         H   H                                                                                  ##STR77##                                            CH.sub.3                                                                            3-CH.sub.3                                                                         6-CH.sub.3                                                                         H   H   CH.sub.2OCH.sub.3                                     CH.sub.3                                                                            3-CH.sub.3                                                                         6-CH.sub.3                                                                         H   H                                                                                  ##STR78##                                            CH.sub. 3                                                                           3-CH.sub.3                                                                         6-CH.sub.3                                                                         H   H                                                                                  ##STR79##                                            CH.sub.3                                                                            3-CH.sub.3                                                                         6-CH.sub.3                                                                         H   H   CH.sub.2OC.sub.2 H.sub.5                              CH.sub.3                                                                            3-CH.sub.3                                                                         6-CH.sub.3                                                                         H   H   CH.sub.2OSO.sub.2 CH.sub.3                            CH.sub.3                                                                            3-CH.sub.3                                                                         6-CH.sub.3                                                                         H   H   CHCl.sub.2                                            CH.sub.3                                                                            3-CH.sub.3                                                                         6-CH.sub.3                                                                         H   H   COOCH.sub.3                                           CH.sub.3                                                                            3-CH.sub.3                                                                         6-CH.sub.3                                                                         H   H                                                                                  ##STR80##                                            CH.sub.3                                                                            3-CH.sub.3                                                                         6-CH.sub.3                                                                         H   H   CH.sub.2SCH.sub.3                                     CH.sub.3                                                                            3-CH.sub.3                                                                         6-CH.sub.3                                                                         H   H                                                                                  ##STR81##                                            CH.sub.3                                                                            3-CH.sub.3                                                                         6-CH.sub.3                                                                         H   H   CHCH.sub.2                                            __________________________________________________________________________

The invention also provides a process for the preparation of anN-allenyl-acetanilide of the formula (I) in which anN-propargyl-acetanilide of the general formula ##STR82## in which R¹ toR⁶ have the meanings indicated above, is subjected to a rearrangementreaction in the presence of a base, as a catalyst, and if appropriate inthe presence of a diluent.

If, for example, 2,6-dimethyl-N-(2-furoyl)-N-propargyl-aniline is usedas the starting material and potassium tert.-butylate is used as thebase, the course of the reaction can be represented by the following##STR83##

The formula (II) provides a general definition of theN-propargylacetanilides required as starting materials in carrying outthe process according to the invention. In this formula, R¹, R², R³, R⁴,R⁵ and R⁶ preferably have those meanings which have already beenmentioned as preferred in connection with the description of thecompounds of the formula (I).

The N-propargyl-acetanilides of the formula (II) have not hitherto beendescribed in the literature; however, they are the subject of U.S.Patent application Ser. No. 83,875, abandoned.

The N-propargyl-acetanilides of the formula (II) can be obtained by theprocess described therein, for example by a procedure in which

(a) propargyl-anilines of the general formula ##STR84## in which R¹ toR⁵ have the meanings indicated above, are reacted with acid chlorides,bromides or anhydrides of the formula ##STR85## in which R⁶ has themeaning indicated above, in the presence of an inert solvent, forexample tetrahydrofuran, and if appropriate in the presence of anacid-binding agent, for example triethylamine or pyridine, at atemperature between 20° and 100° C., or

(b) anilides of the general formula ##STR86## in which R¹, R², R³ and R⁶have the meanings indicated above, are reacted with propargyl halides ofthe general formula ##STR87## in which

R⁴ and R⁵ have the meanings indicated above and

Hal represents chlorine or bromine, preferably in an aqueous-organictwo-phase system, for example aqueous sodium hydroxide solution orpotassium hydroxide solution/toluene or methylene chloride, ifappropriate with the addition of 0.1-1 mole of phase transfer catalyst,for example triethyl-benzyl-ammonium chloride, at a temperature between-20° and -80° C.

N-Propargyl-anilines of the formula (III) are known (see U.S. Pat. Nos.3,535,377 and 4,001,325); they can all be obtained by known processes,for example by reacting corresponding anilines with propargyl halides ofthe formula (VI) or the corresponding propargyl sulphones, for examplemesylates or tosylates, in the presence of an acid-binding agent, forexample sodium carbonate or potassium carbonate, if appropriate in thepresence of an inert organic solvent, for example ethanol, at atemperature between 20° and 150° C., it also being possible, preferably,to employ an excess of aniline.

N-Propargyl-anilines of the formula (III) in which R⁴ represents methylcan also be obtained by reacting the corresponding anilines withacetylene in the presence of copper acetylide under pressure (in thiscontext, see Liebigs Ann, Chem. 596 1 (1955)).

The anilides of the formula (V) can be obtained in a generally knownmanner, by reacting corresponding anilines with an acid chloride,bromide or anhydride of the formula (IVa) or (IVb) under the conditionsof process (a) above, in the presence of an inert organic solvent, forexamle toluene or methylene chloride, if appropriate in the presence ofan acid-binding agent, for example potassium carbonate or triethylamine,or in the presence of a catalyst, for example dimethylformamide, at atemperature between 0° and 100° C.

The acid chlorides, bromides and anhydrides of the formulae (IVa) and(IVb) and the propargyl halides of the formula (VI) are generally knowncompounds of organic chemistry.

Examples which may be mentioned of the N-propargylacetanilides of theformula (II) to be used as starting materials for the process accordingto the invention are:

    ______________________________________                                         ##STR88##                    (II)                                                                                    Melting                               R.sup.1                                                                            R.sup.2 R.sup.3                                                                             R.sup.4                                                                           R.sup.5                                                                            R.sup.6     point (°C.)                    ______________________________________                                        CH.sub.3                                                                           6-CH.sub.3                                                                            H     H   H                                                                                   ##STR89##  109-12                                CH.sub.3                                                                           6-CH.sub.3                                                                            H     H   H    CH.sub.2OCH.sub.3                                                                         49-51                                 C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                     H     H   H                                                                                   ##STR90##  129-31                                CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                     H     H   H                                                                                   ##STR91##  129-31                                CH.sub.3                                                                           6-CH.sub.3                                                                            H     H   CH.sub.3                                                                            ##STR92##  110-12                                CH.sub.3                                                                           6-CH.sub.3                                                                            H     H   H                                                                                   ##STR93##  120-21                                CH.sub.3                                                                           6-CH.sub.3                                                                            H     H   H                                                                                   ##STR94##  137-40                                CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                     H     H   H                                                                                   ##STR95##  88                                    CH.sub.3                                                                           6-CH.sub.3                                                                            H     H   CH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                        n.sub. D.sup. 20  : 1,5362                                                    boiling point                                                                 125/0.1 mbar                          C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                     H     H   H    CH.sub.2 OCH.sub.3                                                                        74                                    CH.sub.3                                                                           6-CH.sub.3                                                                            H     H   H    CHCl.sub.2  114-15                                C.sub.2 H.sub.5                                                                    6-CH.sub.3                                                                            H     H   H                                                                                   ##STR96##  98-99                                 Cl   6-CH.sub.3                                                                            H     H   H    CH.sub.2 OCH.sub.3                                                                        80                                    CH.sub.3                                                                           6-CH.sub.3                                                                            H     H   H                                                                                   ##STR97##  93-94                                 ______________________________________                                    

Preferred diluents for the reaction according to the invention are inertorganic solvents. These include, as preferences, ethers, such astetrahydrofuran or dioxane; alcohols, such as methanol, ethanol ortert.-butanol; and dimethylsulphoxide.

The process according to the invention is carried out in the presence ofa base, as a catalyst. Bases which are preferably used here are alkalimetal hydroxides or alkali metal carbonates, for example sodiumhydroxide or carbonate or potassium hydroxide or carbonate, andespecially alkali metal alcoholates, for example sodium methylate,sodium ethylate or potassium tert.-butylate.

The reaction temperatures can be varied within a substantial range incarrying out the process according to the invention. In general, theprocess is carried out at from 0° to 120° C., preferably from 20° to 80°C.

The active compounds according to the invention exhibit a powerfulmicrobicidal action and can be employed in practice for combatingundesired micro-organisms. The active compounds are suitable for use asplant protection agents.

Fungicidal agents in plant protection are employed for combatingPlasmodioophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

The good toleration, by plants, of the active compounds, at theconcentrations required for combating plant diseases, permits treatmentof above-ground parts of plants of vegetative propagation stock andseeds, and of the soil.

As plant protection agents, the active compounds according to theinvention can be used with particularly good success for combatingOomycetes, for example the pathogen of blight and brown rot of tomatoand potato (Phytophthora infestans). It should be particularlyemphasized that the active compounds according to the invention developnot only a protective action but also a curative/eradicative action.They also have systemic properties. Thus, it is possible to protectplants against fungal attack when the active compound is fed to theabove-ground parts of the plant via the soil and the roots or via theseed.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, suspensions, powders, dusting agents,foams, pastes, soluble powders, granules, aerosols, suspension-emulsionconcentrates, seed-treatment powders, natural and synthetic materialsimpregnated with active compound, very fine capsules in polymericsubstances, coating compositions for use on seed, and formulations usedwith burning equipment, such as fumigating cartridges, fumigating cansand fumigating coils, as well as ULV cold mist and warm mistformulations.

These formulations may be produced in known manner, for example bymixing the active compounds with extenders, that is to say liquid orliquefied gaseous or solid diluents or carriers, optionally with the useof surface-active agents, that is to say emulsifying agents and/ordispersing agents and/or foam-forming agents. In the case of the use ofwater as an extender, organic solvents can, for example, also be used asauxiliary solvents.

As liquid diluents or carriers, especially solvents, there are suitablein the main, aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic or alicyclic hydrocarbons, such as cyclohexane orparaffins, for example mineral oil fractions, alcohols, such as butanolor glycol as well as their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, orstrongly polar solvents, such as dimethylformamide anddimethylsulphoxide, as well as water.

By liquefied gaseous diluents or carriers are meant liquids which wouldbe gaseous at normal temperature and under normal pressure, for exampleaerosol propellants, such as halogenated hydrocarbons as well as butane,propane, nitrogen and carbon dioxide.

As solid carriers there may be used ground natural minerals, such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic materials, such ashighly-dispersed silicic acid, alumina and silicates. As solid carriersfor granules there may be used crushed and fractionated natural rockssuch as calcite, marble, pumice, sepiolite and dolomite, as well assynthetic granules of inorganic and organic meals, and granules oforganic material such as sawdust, coconut shells, corn cobs and tobaccostalks.

As emulsifying and/or foam-forming agents there may be used non-ionicand anionic emulsifiers, such as polyoxyethylene-fatty acid esters,polyoxyethylene-fatty alcohol ethers, for exaple alkylaryl polyglycolethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well asalbumin hydrolysis products. Dispersing agents include, for example,lignin sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, can be used in theformulations.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs or metal phthalocyaninedyestuffs, and trace nutrients, such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain from 0.1 to 95 percent by weight ofactive compound, preferably from 0.5 to 90 percent by weight.

The active compounds according to the invention can be present in theformulations or in the various use forms as a mixture with other activecompounds, such as fungicides, bactericides, insecticides, acaricides,nematicides, herbicides, bird repellants, growth factors, plantnutrients and agents for improving soil structure.

The active compounds can be used as such or in the form of theirformulations or the use forms prepared therefrom by further dilution,such as ready-to-use solutions, emulsions, suspensions, powders, pastesand granules. They can be used in the customary mannner, for example bywatering, immersion, spraying, atomizing, misting, vaparizing,injecting, forming a slurry, brushing on, dusting, scattering, drydressing, moist dressing, wet dressing, slurry dressing or encrusting.

Especially in the treatment of parts of plants, the active compoundconcentrations in the use forms can be varied within a substantialrange. They are, in general, from 1 to 0.0001% by weight, preferablyfrom 0.5 to 0.001%.

In the treatment of seed, amounts of active compound of, in general,0.001 to 50 g, preferably 0.01 to 10 g, are generally employed perkilogram of seed.

For the treatment of soil, active compound concentrations of, ingeneral, 0.0001 to 0.1% by weight, preferably 0.0001 to 0.02%, areemployed at the place of action.

The present invention also provides a fungicidal composition containingas active ingredient a compound of the present invention in admixturewith a solid or liquefied gaseous diluent or carrier or in admixturewith a liquid diluent or carrier containing a surface-active agent.

The present invention also provides a method of combating fungi whichcomprises applying to the fungi, or to a habitat thereof, a compound ofthe present invention alone or in the form of a composition containingas active ingredient a compound of the present invention in admixturewith a diluent or carrier.

The present invention further provides crops protected from damage byfungi by being grown in areas in which immediately prior to and/orduring the time of the growing a compound of the present invention wasapplied alone or in admixture with a diluent or carrier.

It will be seen that the usual methods of providing a harvested crop maybe improved by the present invention.

The preparation of the novel compounds is shown in the followingillustrative examples:

EXAMPLE 1 ##STR98##

50 g (0.2 mol) of 2,6-dimethyl-N-(2-furoyl)-N-propargyl-aniline weredissolved in 200 ml of anhydrous tetrahydrofuran, and 150 mg ofpotassium tert.-butylate were added. During this procedure, thetemperature of the solution rose to about 50° C., the solution becomingcolored. The reaction mixture was left to stand for 2 hours and thenpoured onto 500 ml of water. The crystalline product which hadprecipitated was filtered off, dried and recrystallized from ethylacetate/petroleum ether. 24 g (48% of theory) of2,6-dimethyl-N-allenyl-N-(2-furoyl)-aniline of melting point 138°-41° C.were obtained. (The ¹ H-NMR spectrum indicated complete isomerization).##STR99##

2,6-Dimethyl-N-propargyl-aniline was prepared by reacting2,6-dimethyl-aniline with propargyl bromide according to the statementsin the literature (see U.S. Pat. No. 4,001,325). ##STR100##

15.9 g (0.1 mol) of 2,6-dimethyl-N-propargylaniline and 8 g (0.1 mol) ofpyridine were heated to the boil in 100 ml of tetrahydrofuran, and 13 g(0.1 mol) of furan-2-carboxylic acid chloride were added carefully. Thereaction mixture was stirred under reflux for 15 minutes and thenconcentrated by distilling off the solvent in vacuo. The residue wastaken up in methylene chloride and the methylene chloride mixture waswashed with water. The organic phase was separated off, dried oversodium sulphate and concentrated. After triturating with petroleumether, the residue crystallized. 22.5 g (89% of theory) of2,6-dimethyl-N-(2-furoyl)-N-propargyl-aniline of melting point 109°-112°C. were obtained.

The following compounds of the general formula ##STR101## were obtainedin analogous manner:

EXAMPLE 1

    ______________________________________                                                                                     Melt-                            Com-                                         ing                              pound                                        point                            No.   R.sup.1                                                                              R.sup.2 R.sup.3                                                                           R.sup.4                                                                           R.sup.5                                                                           R.sup.6     (°C.)                     ______________________________________                                        2     CH.sub.3                                                                             6-CH.sub.3                                                                            H   H   H   CH.sub.2 OCH.sub.3                                                                        97-99                            3     CH.sub.3                                                                             6-CH.sub.3                                                                            H   H   H                                                                                  ##STR102## 117-19                           4     CH.sub.3                                                                             6-CH.sub.3                                                                            H   H   H                                                                                  ##STR103## 98-100                           5     Cl     6-CH.sub.3                                                                            H   H   H   CH.sub.2 OCH.sub.3                                                                        95-100                           6     CH.sub.3                                                                             6-CH.sub.3                                                                            H   H   H   CH.sub.2 OC.sub.2 H.sub.5                                                                 59-60                            ______________________________________                                    

The fungicidal activity of the compounds of this invention isillustrated by the following biotest Examples.

In these Examples, the compounds according to the present invention areeach identified by the number (given in brackets) of the correspondingpreparative Example, which will be found later in this specification.

The known comparison compounds are identified as follows: ##STR104##

EXAMPLE A

Phytophthora test (tomato)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

Water: 95 parts by weight

The amount of the active compound required for the desired concentrationof the active compound in the spray liquid was mixed with the statedamount of solvent and the concentrate was diluted with the stated amountof water which contained the stated amount of emulsifier.

Young tomato plants with 2 to 4 foliage leaves were sprayed with thespray liquid until dripping wet. The plants remained in a greenhouse for24 hours at 20 deg.C. and at a relative atmospheric humidity of 70%. Thetomato plants were then inoculated with an aqueous spore suspension ofPhytophthora infestans. The plants were brought into a moist chamberwith an atmospheric humidity of 100% and a temperature of 18-20 deg.C.

After 5 days the infection of the tomato plants was determined. Theassessment data were converted to percent infection: 0% meant noinfection; 100% meant that the plants were totally infected.

In this test, for example, the following compounds exhibited a very goodaction which was significantly superior to that of the compounds (B) and(C) known from the prior art: compounds (1), (2) and (5).

EXAMPLE B

Phytophthora test (tomato)/systemic

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

Water: 95 parts by weight

The amount of active compound required for the desired concentration ofthe active compound in the watering liquid was mixed with the statedamount of solvent and the concentrate was diluted with the stated amountof water which contained the stated amount of the emulsifier.

Tomato plants grown in standard soil and having 2 to 4 foliage leaveswere watered three times in the course of one week with 10 ml of thewatering liquid, having the stated concentration of active compound, per100 ml of soil.

The plants treated in this way were inoculated, after the treatment,with an aqueous spore suspension of Phytophthora infestans. The plantswere brought into a humidity chamber at an atmospheric humidity of 100%and a temperature of 18 to 20 deg.C. After 5 days, the infection of thetomato plants was determined. The assessment data obtained wereconverted to percent infection. 0% denoted no infection and 100% denotedthat the plants were totally infected.

In this test, for example, the following compound exhibited a very goodaction which was significantly superior to that of the compounds (A) and(B) known from the prior art: compound (1).

It will be appreciated that the instant specification and examples areset forth by way of illustration and not limitation, and that variousmodifications and changes may be made without departing from the spiritand scope of the present invention.

We claim:
 1. An N-allenyl-acetanilide of the formula ##STR105## in whichR¹ represents hydrogen, alkyl with up to 4 carbon atoms, or halogen,R²represents hydrogen or alkyl with up to 4 carbon atoms, R³ representshydrogen or alkyl with up to 4 carbon atoms, R⁴ represents hydrogen oralkyl with up to 4 carbon atoms, R⁵ represents hydrogen or alkyl with upto 4 carbon atoms, R⁶ represents furyl, tetrahydrofuryl, thiophenyl ortetrahydrothiophenyl; isoxazolyl which is optionally substituted byalkyl with up to 4 carbon atoms; ##STR106## Az represents pyrazol-1-yl,1,2,4-triazol-1-yl or imidazol-1-yl.
 2. A compound according to claim 1,wherein such compound is2,6-dimethyl-N-allenyl-N-(5-methylisoxazolyl-3-carbonyl)-aniline of theformula ##STR107##
 3. A compound according to claim 1, wherein suchcompound is 2,6-dimethyl-N-allenyl-N-(2-furoyl)-aniline of the formula##STR108##
 4. A compound according to claim 1, wherein such compound is2,6-dimethyl-N-allenyl-N-(1,2,4-triazol-1-yl-acetyl)-aniline ##STR109##5. A fungicidal composition containing as active ingredient afungicidally effective amount of a compound according to claim 1 inadmixture with a diluent.
 6. A method of combating fungi which comprisesapplying to the fungi, or to a habitat thereof, a fungicidally effectiveamount of a compound according to claim
 1. 7. The method according toclaim 6, wherein such compoundis2,6-dimethyl-N-allenyl-N-(2-furoyl)-aniline,2,6-dimethyl-N-allenyl-N-(1,2,4-triazol-1-yl-acetyl)-aniline or2,6-dimethyl-N-allenyl-N-(5-methyl-isoxazolyl-3-carbonyl)-aniline.